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| verifiedrevid = 451606850 |
| verifiedrevid = 451606850 |
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| IUPAC_name = (1-(2- |
| IUPAC_name = (1-(2-Morpholin-4-ylethyl)indol-3-yl)-4-methoxynaphthalen-1-ylmethanone |
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| image = JWH-198.svg |
| image = JWH-198.svg |
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| width = |
| width = 150 |
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<!--Clinical data--> |
<!--Clinical data--> |
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| legal_CA = Schedule II |
| legal_CA = Schedule II |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_US = |
| legal_US = Schedule I |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=26 | H=26 | N=2 | O=3 |
| C=26 | H=26 | N=2 | O=3 |
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| molecular_weight = 414.495 g/mol |
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| smiles = C4COCCN4CCn2cc(c5ccccc25)C(=O)c3c1ccccc1c(OC)cc3 |
| smiles = C4COCCN4CCn2cc(c5ccccc25)C(=O)c3c1ccccc1c(OC)cc3 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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'''JWH-198''' is a drug from the [[aminoalkylindole]] |
'''JWH-198''' is a drug from the [[aminoalkylindole]] and [[naphthoylindole]] families which acts as a [[cannabinoid receptor]] [[agonist]]. It was invented by the pharmaceutical company Sanofi-Winthrop in the early 1990s. JWH-198 has a [[Dissociation constant|binding affinity]] at the CB<sub>1</sub> receptor of 10 nM, binding around four times more tightly than the parent compound [[JWH-200]], which has no substitution on the naphthoyl ring.<ref name="pmid15974991">{{cite journal | vauthors = Huffman JW, Padgett LW | title = Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes | journal = Current Medicinal Chemistry | volume = 12 | issue = 12 | pages = 1395–411 | year = 2005 | pmid = 15974991 | doi = 10.2174/0929867054020864 }}</ref> It has been used mainly in [[molecular modelling]] of the cannabinoid receptors.<ref name="pmid7636873">{{cite journal | vauthors = Eissenstat MA, Bell MR, D'Ambra TE, Alexander EJ, Daum SJ, Ackerman JH, Gruett MD, Kumar V, Estep KG, Olefirowicz EM | title = Aminoalkylindoles: structure-activity relationships of novel cannabinoid mimetics | journal = Journal of Medicinal Chemistry | volume = 38 | issue = 16 | pages = 3094–105 | date = Aug 1995 | pmid = 7636873 | doi = 10.1021/jm00016a013 }}</ref><ref name="pmid9804691">{{cite journal | vauthors = Shim JY, Collantes ER, Welsh WJ, Subramaniam B, Howlett AC, Eissenstat MA, Ward SJ | title = Three-dimensional quantitative structure-activity relationship study of the cannabimimetic (aminoalkyl)indoles using comparative molecular field analysis | journal = Journal of Medicinal Chemistry | volume = 41 | issue = 23 | pages = 4521–32 | date = Nov 1998 | pmid = 9804691 | doi = 10.1021/jm980305c }}</ref> |
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In the United States, all CB<sub>1</sub> receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-198 are [[Schedule I Controlled Substance]]s.<ref>{{UnitedStatesCode2|21|812|Schedules of controlled substances}}</ref> |
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== See also == |
== See also == |
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[[Category:Morpholines]] |
[[Category:Morpholines]] |
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[[Category:Designer drugs]] |
[[Category:Designer drugs]] |
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[[Category:CB1 receptor agonists]] |
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{{cannabinoid-stub}} |
{{cannabinoid-stub}} |
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Revision as of 11:26, 3 August 2019
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| Formula | C26H26N2O3 |
| Molar mass | 414.505 g·mol−1 |
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JWH-198 is a drug from the aminoalkylindole and naphthoylindole families which acts as a cannabinoid receptor agonist. It was invented by the pharmaceutical company Sanofi-Winthrop in the early 1990s. JWH-198 has a binding affinity at the CB1 receptor of 10 nM, binding around four times more tightly than the parent compound JWH-200, which has no substitution on the naphthoyl ring.[1] It has been used mainly in molecular modelling of the cannabinoid receptors.[2][3]
In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-198 are Schedule I Controlled Substances.[4]
See also
References
- ^ Huffman JW, Padgett LW (2005). "Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes". Current Medicinal Chemistry. 12 (12): 1395–411. doi:10.2174/0929867054020864. PMID 15974991.
- ^ Eissenstat MA, Bell MR, D'Ambra TE, Alexander EJ, Daum SJ, Ackerman JH, Gruett MD, Kumar V, Estep KG, Olefirowicz EM (Aug 1995). "Aminoalkylindoles: structure-activity relationships of novel cannabinoid mimetics". Journal of Medicinal Chemistry. 38 (16): 3094–105. doi:10.1021/jm00016a013. PMID 7636873.
- ^ Shim JY, Collantes ER, Welsh WJ, Subramaniam B, Howlett AC, Eissenstat MA, Ward SJ (Nov 1998). "Three-dimensional quantitative structure-activity relationship study of the cannabimimetic (aminoalkyl)indoles using comparative molecular field analysis". Journal of Medicinal Chemistry. 41 (23): 4521–32. doi:10.1021/jm980305c. PMID 9804691.
- ^ : Schedules of controlled substances